Silver-catalyzed monofluoromethylation of alkynoates with sodium monofluoroalkanesulfinate (CH₂FSO₂Na) to access 3-monofluoromethylated coumarins

Recent Methods for Synthesis of Coumarin Derivatives and Their New Applications

“…in DMSO (3.0 mL) and heated to 60°C in an environment of nitrogen for 24 h (Figure 28). The reaction is compatible with both electron-rich and deficient substituents at the para position of phenyl ring [76].…”

The synthetic versatility of fluoroiodomethane: recent applications as monofluoromethylation platform

“…67–70 Although historically underdeveloped compared to trifluoromethylation, and difluoromethylation, different methodologies for the radical monofluoromethylation have been recently introduced. In several reported examples, the fluoromethyl radical could be generated from sulfurated precursors, such as fluoromethylated sulfones, 71 sulfoximines, 72 sulfinates, 73–75 and sulfonyl chlorides, 76,77 via SET (Single-Electron Transfer) processes. However, the activation of these reagents often requires harsh reaction conditions, such as strong oxidants or reductants, or high temperatures, because of the low reactivity of fluoromethylated reagents.…”

Recent Advances in the Synthesis of Coumarin and Its Derivatives by Using Aryl Propiolates

“…Fu et al . in 2019, reported the formation of 3‐monofluoromethylated coumarins 53 (Scheme 31) through monofluoromethylation of substrate 1 and sodium monofluoroalkanesulfinate (CH 2 FSO 2 Na) using Ag as a catalyst [43] . Phenyl alkynoate and monofluoromethyl benzo[ d ]‐thiazol‐2‐yl sulfone for CH 2 F radical source was reacted in the presence of silver nitrate (10 mol %) and potassium persulphate (4.0 equiv.)…”